Sodium Bicarbonate → HCID 56987681, compound

HRID 465458Notes

Reaction equation

HRID 465458 reaction equation
C1CO[C:3]([CH3:18])([CH2:4][C:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][CH:14](O)[CH2:13][CH2:12]3)=[CH:7][CH:6]=2)[O:2]1.C(=O)(O)[O-].[Na+]>Cl>[N:11]1([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C:3](=[O:2])[CH3:18])=[CH:6][CH:7]=2)[CH2:12][CH:13]=[CH:14][CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86746172HCID 86746172, compound

Product 1

HCID 56987681HCID 56987681, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-[4-(2,2-Ethylenedioxypropyl)phenyl piperidin-4-ol (0.9 g) was dissolved in 50% hydrochloric acid solution, and heated under reflux for 4 hr. The solution was cooled, basified with 1.2M sodium bicarbonate solution and extracted with ethylacetate (3×50 ml). The organic extract was dried (magnesium sulphate), filtered and evaporated in vacuo, to give an oil which was chromatographed on silica. Elution with chloroform:methanol (97:3) gave 4-(1,2,3,6-tetrahydropyridyl) phenyl propan-2-one (0.5 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hr
  3. temperatureThe solution was cooled
  4. extractionextracted with ethylacetate (3×50 ml)
  5. extractionThe organic extract
  6. dry with materialwas dried (magnesium sulphate)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give an oil which
  10. customwas chromatographed on silica
  11. washElution with chloroform:methanol (97:3)

Sources & evidence

ORD record
ord-02e9a05e0a9e4406b308d159588cd51e
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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